EP0206076A2 - Acides 4-quinolone-3-carboxyliques pontés sur les positions 1,8, procédé pour leur préparation ainsi que médicaments les contenant et leur utilisation pour la fabrication des médicaments - Google Patents
Acides 4-quinolone-3-carboxyliques pontés sur les positions 1,8, procédé pour leur préparation ainsi que médicaments les contenant et leur utilisation pour la fabrication des médicaments Download PDFInfo
- Publication number
- EP0206076A2 EP0206076A2 EP86107840A EP86107840A EP0206076A2 EP 0206076 A2 EP0206076 A2 EP 0206076A2 EP 86107840 A EP86107840 A EP 86107840A EP 86107840 A EP86107840 A EP 86107840A EP 0206076 A2 EP0206076 A2 EP 0206076A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- carbon atoms
- alkyl
- phenyl
- hydrogen
- optionally substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 0 CCc(cc(c(*(C1)C=C2C(O)=O)c3OC1C1CCCCC1)C2=O)c3F Chemical compound CCc(cc(c(*(C1)C=C2C(O)=O)c3OC1C1CCCCC1)C2=O)c3F 0.000 description 4
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Definitions
- the invention relates to new 1,8-bridged 4-quinolone-3-carboxylic acids, a process for their preparation and their use as medicaments, in particular as antibacterial agents in human and veterinary medicine.
- the phenyl radicals can be substituted by halogen, alkyl having 1-3 carbon atoms, nitro, cyano, alkoxy or alkylmercapto having 1-3 carbon atoms, phenoxy, phenylthio or an ester group having 1-3 carbon atoms in the alcohol part.
- R 1 -R 6 The 3-7-membered rings formed by R 1 -R 6 can be substituted by alkyl radicals with 1-3 carbon atoms or phenyl radicals.
- diethyl malonate (2) is acylated in the presence of magnesium ethylate with the corresponding benzoyl fluoride or chloride (1) to give the benzoylmalonic ester (3) (Organicum, 3rd edition 1964, p. 438).
- ethyl benzoylacetate (4) is obtained in good yield, which is converted into ethyl 3-ethoxyacrylic acid (5) with triethyl orthoformate / acetic anhydride.
- Dioxane, dimethyl sulfoxide, N-methylpyrrolidone, sulfolane, hexamethylphosphoric triamide and preferably N, N-dimethylformamide can be used as diluents.
- Potassium tert-butoxide, butyl lithium, lithium phenyl, phenyl magnesium bromide, sodium methylate, sodium hydride, sodium or potassium carbonate and particularly preferably potassium or sodium fluoride are suitable as acid binders for this reaction stage.
- the hydrolysis of the esters (9) to the corresponding carboxylic acids in the last step can be carried out under the customary known acidic or basic conditions.
- the 2,4-dichloro-5-fluoro-3-nitro-benzoyl chloride is converted to 2,4-dichloro-5-fluoro-3-nitro-benzoic acid and the like by nitration of the known 2,4-dichloro-S-fluoro-benzoic acid Receive reaction with thionyl chloride.
- the amines of the formula (6) used as starting materials are known. Examples include: 2-aminocyclopentanol, 2-aminocyclohexanol, 2- (2-aminoethylamino) ethanol, 2-amino-2-phenylethanol, 1-amino-2,3-propanediol, 2-amino-3-phenylpropanol , 2-amino-1-phenyl-1,3-propanediol, N-phenylethylene diamine, N-benzylethylene diamine, 2-aminomethylcyclohexanol.
- acid binders are all customary inorganic and organic sheurebindun can be used g skar. These preferably include the alkali metal hydroxides, alkali metal carbonates, organic amines and amidines. The following may be mentioned as particularly suitable: triethylamine, 1,4-diaza-bicvclo [2,2,2] octane (DABCO), 1,8-diazabicyclo [5,4,0] -undec-7-ene (DBU ) or excess amine (III).
- DABCO 1,4-diaza-bicvclo [2,2,2] octane
- DBU 1,8-diazabicyclo [5,4,0] -undec-7-ene
- III excess amine
- reaction temperatures can be varied within a wide range. Generally one works between about 20 and 200 ° C, preferably between 80 and 180 ° C.
- the reaction can be carried out at normal pressure, but also at elevated pressure. Generally one works at pressures between about 1 and about 100 bar, preferably between 1 and 10 bar.
- reaction of (IV) with (V) is preferably carried out in a diluent such as dimethyl sulfoxide, dioxane, N, N-dimethylformamide, hexamethylphosphoric acid trisamide, sulfolane, water, an alcohol such as methanol, ethanol, n-propanol, isopropanol, glycol monomethyl ether or pyridine. Mixtures of these diluents can also be used.
- a diluent such as dimethyl sulfoxide, dioxane, N, N-dimethylformamide, hexamethylphosphoric acid trisamide, sulfolane, water, an alcohol such as methanol, ethanol, n-propanol, isopropanol, glycol monomethyl ether or pyridine.
- acid binders can be used as acid binders. These preferably include the alkali metal hydroxides, alkali metal carbonates, organic amines and amidines. The following may be mentioned as particularly suitable: triethylamine, 1,4-diazabicyclo [2,2,2] octane (DABCO) or 1,8-diazabicyclo- [5,4,0] undec-7-ene (DBU).
- DABCO 1,4-diazabicyclo [2,2,2] octane
- DBU 1,8-diazabicyclo- [5,4,0] undec-7-ene
- reaction temperatures can be varied within a wide range. Generally one works between about 20 and about 180 ° C, preferably between 40 and 110 ° C.
- the reaction can be carried out at normal pressure, but also at elevated pressure. Generally one works at pressures between about 1 and about 100 bar, preferably between 1 and 10 bar.
- reaction of (IV) with (VI) is preferably carried out in a diluent such as dioxane, dimethyl sulfoxide, N, N-dimethylformamide, methanol, ethanol, isopropanol, n-propanol, glycol monomethyl ether or in mixtures of these diluents.
- a diluent such as dioxane, dimethyl sulfoxide, N, N-dimethylformamide, methanol, ethanol, isopropanol, n-propanol, glycol monomethyl ether or in mixtures of these diluents.
- reaction temperatures can be varied within a wide range. Generally one works between about 20 ° C and about 150 ° C, preferably between 50 ° C and 100 ° C.
- the reaction can be carried out at normal pressure, but also at elevated pressure. Generally one works at pressures between about 1 and about 100 bar, preferably between 1 and 10 bar.
- Each tablet contains:
- the lacquer cover contains:
- the compounds according to the invention show a broad antibacterial spectrum against gram-positive and gram-negative germs, in particular against enterobacteriaceae: above all also against those which are resistant to various antibiotics, such as e.g. Penicillins, cephalosporins, aminoglycosides, sulfonamides, tetracyclines.
- antibiotics such as e.g. Penicillins, cephalosporins, aminoglycosides, sulfonamides, tetracyclines.
- chemotherapeutic active compounds in medicine and as substances for preserving inorganic and or g ANI's materials, especially organic materials of all kinds, for example polymers, lubricants, paints, fibers, leather, paper and wood, and Food and water.
- the compounds according to the invention are active against a very broad spectrum of microorganisms. With their help, gram-negative and gram-positive bacteria and bacterial-like microorganisms can be combated and the diseases caused by these pathogens can be prevented, improved and / or cured.
- the compounds according to the invention are particularly effective against bacteria and bacterial-like microorganisms. They are therefore particularly well suited for the prophylaxis and chemotherapy of local and systemic infections in human and veterinary medicine, which are caused by these pathogens.
- the present invention includes pharmaceutical preparations which, in addition to non-toxic, inert pharmaceutically suitable excipients, contain one or more compounds according to the invention or which consist of one or more active compounds according to the invention, and processes for producing these preparations.
- the present invention also includes pharmaceutical preparations in dosage units.
- the Dosierun g s-units can, for example, 1, 2, 3 or 4 individual doses or 1/2, 1/3 or 1/4 contain a single dose.
- a single dose preferably contains the amount of active ingredient which is administered in one application and which usually corresponds to a whole, a half or a third or a quarter of a daily dose.
- Non-toxic, inert pharmaceutically suitable carriers are to be understood as solid, semi-solid or liquid diluents, fillers and formulation auxiliaries of all kinds.
- Tablets, dragees, capsules, pills, granules, suppositories, solutions, suspensions and emulsions, pastes, ointments, gels, creams, lotions, powders and sprays may be mentioned as preferred pharmaceutical preparations.
- Tablets, coated tablets, capsules, pills and granules can contain the active ingredient (s) in addition to the usual carriers contain, such as (a) fillers and extenders, for example starches, milk sugar, cane sugar, glucose, mannitol and silica. (b) binders, e.g. carboxymethyl cellulose, alginates, gelatin, polyvinylpyrrolidone, (c) humectants, e.g. glycerol, (d) disintegrants, e.g. agar-agar, calcium carbonate and sodium carbonate, (e) dissolution retarders, e.g. paraffin and (f) resorption accelerators, e.g.
- fillers and extenders for example starches, milk sugar, cane sugar, glucose, mannitol and silica.
- binders e.g. carboxymethyl cellulose, alginates, gelatin, polyvinylpyrrolidone
- humectants e.
- quaternary ammonium compounds (g) wetting agents, e.g. cetyl alcohol, glycerol monostearate, (h) adsorbents, e.g. kaolin and bentonite and (i) lubricants e.g. talc, calcium and magnesium stearate and solid polyethylene glycols or mixtures of the substances listed under (a) to (i) .
- wetting agents e.g. cetyl alcohol, glycerol monostearate
- adsorbents e.g. kaolin and bentonite
- lubricants e.g. talc, calcium and magnesium stearate and solid polyethylene glycols or mixtures of the substances listed under (a) to (i) .
- the tablets, dragees, capsules, pills and granules can be provided with the usual coatings and casings, optionally containing opacifying agents, and can also be composed such that they release the active ingredient (s) only or preferably in a certain part of the intestinal tract, if necessary with a delay, where as embedding compounds e.g. Polymer substances and waxes can be used.
- embedding compounds e.g. Polymer substances and waxes can be used.
- the active ingredient (s) can optionally also be in microencapsulated form with one or more of the above-mentioned excipients.
- suppositories can contain the usual water-soluble or water-insoluble carriers, for example polyethylene glycols, fats, for example cocoa fat and higher esters (for example C 14 alcohol with C 16 fatty acid) or mixtures of these substances.
- water-soluble or water-insoluble carriers for example polyethylene glycols, fats, for example cocoa fat and higher esters (for example C 14 alcohol with C 16 fatty acid) or mixtures of these substances.
- ointments, pastes, creams and gels can contain the usual carriers, e.g. animal and vegetable fats, waxes, paraffins, starch, tragacanth, cellulose derivatives, polyethylene glycols, silicones. Bentonite, silica, talc and zinc oxide or mixtures of these substances.
- Powders and sprays can contain the usual excipients in addition to the active ingredient (s), e.g. Milk sugar, talc. Silicic acid, aluminum hydroxide, calcium silicate and polyamide powder or mixtures of these substances. Sprays can also contain the usual propellants, e.g. Chlorofluorocarbons.
- solutions and emulsions can contain the usual carriers such as solvents, solubilizers and emulsifiers, e.g. Water, ethyl alcohol, isopropyl alcohol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3-butylene glycol, dimethylformamide, oils, in particular cottonseed oil, peanut oil, corn oil, olive oil, castor oil and sesame oil, glycerin, glycerol formaldehyde, tetrahydrofuran fatty acid, tetrahydrofuran fatty acid, tetrahydrofuran fatty acid, tetrahydrofuran or mixtures of these substances.
- solvents e.g. Water, ethyl alcohol, isopropyl alcohol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, prop
- solutions and emulsions can also be in sterile and blood isotonic form.
- suspensions can contain the customary excipients such as liquid diluents, for example water, ethyl alcohol, propylene glycol, suspending agents, for example ethoxylated isostearyl alcohols, polyoxyethylene sensor contain bit and sorbitan esters, microcrystalline cellulose, aluminum metahydroxide, bentonite, agar agar and tragacanth or mixtures of these substances.
- liquid diluents for example water, ethyl alcohol, propylene glycol
- suspending agents for example ethoxylated isostearyl alcohols
- polyoxyethylene sensor contain bit and sorbitan esters, microcrystalline cellulose, aluminum metahydroxide, bentonite, agar agar and tragacanth or mixtures of these substances.
- the formulation forms mentioned can also contain colorants, preservatives and additives which improve the smell and taste, e.g. Peppermint oil and eucalyptus oil and sweeteners, e.g. Saccharin.
- the therapeutically active compounds should be present in the abovementioned pharmaceutical preparations vorzu g s-wise in a concentration of about 0.1 to 99.5, preferably be present from about 0.5 to 95 wt .-% of the total mixture.
- the pharmaceutical preparations listed above can also contain further active pharmaceutical ingredients.
- the pharmaceutical preparations listed above are prepared in a conventional manner by known methods, e.g. by mixing the active substance or substances with the carrier substance or substances.
- the active compounds or the pharmaceutical preparations can be administered locally, orally, parenterally, intraperitoneally and / or rectally, preferably orally or parenterally, such as intravenously or intramuscularly.
- the active compound (s) according to the invention in total amounts of from about 0.5 to about 500, preferably 5 to 100 mg / kg of body weight per 24 hours, if appropriate in the form multiple one to administer the desired results.
- a single dose contains the active ingredient (s) according to the invention, preferably in amounts of about 1 to about 250, in particular 3 to 60 mg / kg of body weight.
- the new compounds may be added in the customary concentrations and formulations together with the feed or with Futterzurun g s or drinking water. Thereby, an infection caused by gram-negative or gram-positive bacteria prevented, alleviated and / or e-g are heals and thereby the chuck to achieve a promotion of growth, and an improvement of utilization.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3522405 | 1985-06-22 | ||
DE19853522405 DE3522405A1 (de) | 1985-06-22 | 1985-06-22 | 1,8-verbrueckte 4-chinolon-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende arzneimittel und ihre verwendung zur herstellung von arzneimitteln |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0206076A2 true EP0206076A2 (fr) | 1986-12-30 |
EP0206076A3 EP0206076A3 (fr) | 1988-07-27 |
Family
ID=6273929
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP86107840A Withdrawn EP0206076A3 (fr) | 1985-06-22 | 1986-06-09 | Acides 4-quinolone-3-carboxyliques pontés sur les positions 1,8, procédé pour leur préparation ainsi que médicaments les contenant et leur utilisation pour la fabrication des médicaments |
Country Status (17)
Country | Link |
---|---|
US (1) | US4847375A (fr) |
EP (1) | EP0206076A3 (fr) |
JP (1) | JPS62490A (fr) |
KR (1) | KR870000337A (fr) |
CN (1) | CN86104256A (fr) |
AU (1) | AU564013B2 (fr) |
DE (1) | DE3522405A1 (fr) |
DK (1) | DK291886A (fr) |
ES (3) | ES8802301A1 (fr) |
FI (1) | FI862640A (fr) |
GR (1) | GR861602B (fr) |
HU (1) | HU195662B (fr) |
IL (1) | IL79163A0 (fr) |
NO (1) | NO862198L (fr) |
NZ (1) | NZ216598A (fr) |
PT (1) | PT82802B (fr) |
ZA (1) | ZA864604B (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0253235A1 (fr) * | 1986-07-15 | 1988-01-20 | Bayer Ag | Acides 4-quinolone carboxyliques pontés sur les positions 1,8 et médicaments les contenant |
EP0391132A1 (fr) * | 1989-04-03 | 1990-10-10 | Bayer Ag | Acides alkyl-5-quinoléinone-carboxyliques |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0228178A (ja) * | 1988-04-23 | 1990-01-30 | Toyama Chem Co Ltd | 新規なピリドンカルボン酸誘導体およびその塩並びにそれらの製造法 |
US5286723A (en) * | 1988-08-31 | 1994-02-15 | Daiichi Seiyaku Co., Ltd. | Spiro compound |
JPH10127313A (ja) * | 1996-10-31 | 1998-05-19 | Ykk Corp | 自動停止装置付スライドファスナー用スライダー |
US6673793B2 (en) | 2000-07-12 | 2004-01-06 | Pharmacia & Upjohn Co. | Oxazinoquinolones useful for the treatment of viral infections |
JP3927922B2 (ja) | 2003-05-21 | 2007-06-13 | Ykk株式会社 | スライドファスナー用スプリング体及び同スプリング体が装着されたスライダー |
MX2008011633A (es) * | 2006-03-13 | 2008-12-16 | Activx Biosciences Inc | Aminoquinolonas como inhibidores de gsk-3. |
CN101855228B (zh) * | 2007-09-11 | 2012-10-24 | 杏林制药株式会社 | 作为gsk-3抑制剂的氰基氨基喹诺酮和四唑并氨基喹诺酮 |
JP5373799B2 (ja) | 2007-09-12 | 2013-12-18 | 杏林製薬株式会社 | Gsk−3阻害剤としてのスピロ環式アミノキノロン |
JP5502889B2 (ja) * | 2009-03-11 | 2014-05-28 | 杏林製薬株式会社 | gsk−3阻害剤としての7−シクロアルキルアミノキノロン |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57149286A (en) * | 1981-03-13 | 1982-09-14 | Dai Ichi Seiyaku Co Ltd | 8-aminopyrido(1,2,3-de)(1,4)banzoxazine derivative |
JPS57210092A (en) * | 1981-06-10 | 1982-12-23 | Benckiser Knapsack Gmbh | Deinking of used paper |
EP0101829A2 (fr) * | 1982-06-29 | 1984-03-07 | Daiichi Seiyaku Co., Ltd. | Composés tricycliques, procédé pour leur préparation et compositions pharmaceutiques les contenant |
EP0107201A2 (fr) * | 1982-10-25 | 1984-05-02 | Riker Laboratories, Incorporated | Agents antibactériens tricycliques substitués par phényle |
EP0115334A1 (fr) * | 1983-01-26 | 1984-08-08 | Otsuka Pharmaceutical Co., Ltd. | Composés benzo-hétérocycliques |
US4473568A (en) * | 1983-03-01 | 1984-09-25 | Warner Lambert Company | Antibacterial thiazolidine or thiomorpholine substituted quinolines |
EP0047005B1 (fr) * | 1980-09-02 | 1984-11-14 | Daiichi Seiyaku Co., Ltd. | Dérivés de benzoxazine |
EP0160284A1 (fr) * | 1984-04-26 | 1985-11-06 | Abbott Laboratories | Composés de quino-benzoxazine antibactériens |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4571396A (en) * | 1984-04-16 | 1986-02-18 | Warner-Lambert Company | Antibacterial agents |
US4771054A (en) * | 1985-01-23 | 1988-09-13 | Warner-Lambert Company | Antibacterial agents |
DE3522406A1 (de) * | 1985-06-22 | 1987-01-02 | Bayer Ag | Verfahren zur herstellung von 1,8-verbrueckten 4-chinolon-3-carbonsaeuren |
DE3600891A1 (de) * | 1986-01-15 | 1987-07-16 | Bayer Ag | 1,8-verbrueckte 4-chinolon-3-carbonsaeuren und diese enthaltende arzneimittel |
-
1985
- 1985-06-22 DE DE19853522405 patent/DE3522405A1/de not_active Withdrawn
-
1986
- 1986-06-03 NO NO862198A patent/NO862198L/no unknown
- 1986-06-09 EP EP86107840A patent/EP0206076A3/fr not_active Withdrawn
- 1986-06-13 US US06/874,249 patent/US4847375A/en not_active Expired - Fee Related
- 1986-06-19 NZ NZ216598A patent/NZ216598A/xx unknown
- 1986-06-19 IL IL79163A patent/IL79163A0/xx unknown
- 1986-06-19 FI FI862640A patent/FI862640A/fi not_active Application Discontinuation
- 1986-06-20 HU HU862603A patent/HU195662B/hu not_active IP Right Cessation
- 1986-06-20 ES ES556369A patent/ES8802301A1/es not_active Expired
- 1986-06-20 PT PT82802A patent/PT82802B/pt unknown
- 1986-06-20 GR GR861602A patent/GR861602B/el unknown
- 1986-06-20 ZA ZA864604A patent/ZA864604B/xx unknown
- 1986-06-20 DK DK291886A patent/DK291886A/da unknown
- 1986-06-20 JP JP61143149A patent/JPS62490A/ja active Pending
- 1986-06-21 KR KR1019860004971A patent/KR870000337A/ko not_active Application Discontinuation
- 1986-06-21 CN CN198686104256A patent/CN86104256A/zh active Pending
- 1986-06-23 AU AU59207/86A patent/AU564013B2/en not_active Ceased
-
1987
- 1987-09-15 ES ES557728A patent/ES8801921A1/es not_active Expired
- 1987-09-15 ES ES557727A patent/ES8802050A1/es not_active Expired
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0047005B1 (fr) * | 1980-09-02 | 1984-11-14 | Daiichi Seiyaku Co., Ltd. | Dérivés de benzoxazine |
JPS57149286A (en) * | 1981-03-13 | 1982-09-14 | Dai Ichi Seiyaku Co Ltd | 8-aminopyrido(1,2,3-de)(1,4)banzoxazine derivative |
JPS57210092A (en) * | 1981-06-10 | 1982-12-23 | Benckiser Knapsack Gmbh | Deinking of used paper |
EP0101829A2 (fr) * | 1982-06-29 | 1984-03-07 | Daiichi Seiyaku Co., Ltd. | Composés tricycliques, procédé pour leur préparation et compositions pharmaceutiques les contenant |
EP0107201A2 (fr) * | 1982-10-25 | 1984-05-02 | Riker Laboratories, Incorporated | Agents antibactériens tricycliques substitués par phényle |
EP0115334A1 (fr) * | 1983-01-26 | 1984-08-08 | Otsuka Pharmaceutical Co., Ltd. | Composés benzo-hétérocycliques |
US4473568A (en) * | 1983-03-01 | 1984-09-25 | Warner Lambert Company | Antibacterial thiazolidine or thiomorpholine substituted quinolines |
EP0160284A1 (fr) * | 1984-04-26 | 1985-11-06 | Abbott Laboratories | Composés de quino-benzoxazine antibactériens |
Non-Patent Citations (2)
Title |
---|
CHEMICAL ABSTRACTS, vol. 98, 1983, page 635, abstract. no. 72117q, Columbus, Ohio, US; DAIICHI SEIYAKU CO., LTD. "8-Aminopyrido[1,2,3-deÜ[1,4Übenzoxazines", & JP - A - 57 149 286 (JPN. KOKAI TOKKYO KOHO) 14-09-1982 * |
PATENT ABSTRACTS OF JAPAN, Band 8, Nr. 52 (C-213)[1489], 9. März 1984; & JP - A - 57 210 092 (DAIICHI SEIYAKU K.K.)07.12.1983 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0253235A1 (fr) * | 1986-07-15 | 1988-01-20 | Bayer Ag | Acides 4-quinolone carboxyliques pontés sur les positions 1,8 et médicaments les contenant |
US4816451A (en) * | 1986-07-15 | 1989-03-28 | Bayer Aktiengesellschaft | Antibacterial 1,8-bridged 4-quinolonecarboxylic acids |
EP0391132A1 (fr) * | 1989-04-03 | 1990-10-10 | Bayer Ag | Acides alkyl-5-quinoléinone-carboxyliques |
Also Published As
Publication number | Publication date |
---|---|
ES8802301A1 (es) | 1988-05-01 |
IL79163A0 (en) | 1986-09-30 |
NZ216598A (en) | 1989-07-27 |
GR861602B (en) | 1986-10-20 |
ES8802050A1 (es) | 1988-03-16 |
EP0206076A3 (fr) | 1988-07-27 |
DE3522405A1 (de) | 1987-01-02 |
CN86104256A (zh) | 1987-03-18 |
DK291886A (da) | 1986-12-23 |
ES557727A0 (es) | 1988-03-16 |
FI862640A0 (fi) | 1986-06-19 |
JPS62490A (ja) | 1987-01-06 |
KR870000337A (ko) | 1987-02-17 |
AU564013B2 (en) | 1987-07-30 |
NO862198D0 (no) | 1986-06-03 |
PT82802A (en) | 1986-07-01 |
ES557728A0 (es) | 1988-03-01 |
ES556369A0 (es) | 1988-05-01 |
ES8801921A1 (es) | 1988-03-01 |
AU5920786A (en) | 1987-02-05 |
HU195662B (en) | 1988-06-28 |
US4847375A (en) | 1989-07-11 |
HUT44256A (en) | 1988-02-29 |
ZA864604B (en) | 1987-02-25 |
DK291886D0 (da) | 1986-06-20 |
NO862198L (no) | 1986-12-23 |
PT82802B (en) | 1988-05-23 |
FI862640A (fi) | 1986-12-23 |
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